Road to Perdition (2002) - Tom Hanks, Daniel Craig

In 1931, during the Great Depression, Michael Sullivan, Sr. is an enforcer for Irish mob boss John Rooney in Rock Island, Illinois. Rooney raised the orphan Sullivan and loves him more than his own biological son, Connor. Rooney sends Connor and Sullivan to meet with disgruntled associate Finn McGovern, but Connor shoots McGovern, resulting in Sullivan gunning down McGovern's men. Sullivan's twelve-year-old son Michael Jr. has hidden in his father's car and witnesses the event. Despite Sullivan swearing his son to secrecy and Rooney pressuring Connor to apologize for the reckless action, Connor murders Sullivan's wife Annie and younger son Peter. At the same time, he sends Sullivan to an ambush at a speakeasy. Sullivan realizes it's a set-up, kills two men at the bar, and escapes. He goes to Chicago with his son to seek Al Capone, for work and to discover the location of Connor, who has gone into hiding.

Capone's underboss Frank Nitti rejects Sullivan's proposals, before informing Rooney of the meeting. Rooney reluctantly allows Nitti to dispatch assassin Harlen Maguire, who is also a crime scene photographer, to kill Sullivan. Maguire tracks him and his son to a roadside diner, but fails to kill Sullivan; realizing Maguire's intentions, Sullivan escapes through the bathroom and punctures Maguire's car tire before fleeing.

In reaction to the ordered hit, Sullivan begins robbing banks that hold Capone’s money, hoping to trade it for Connor. Sullivan is impeded when the mob withdraws its money, so he visits Rooney's accountant Alexander Rance at his hotel. The encounter is a set-up, with Rance stalling Sullivan until Maguire enters with a shotgun. In the ensuing crossfire, Rance is killed, Maguire is injured by flying glass shards, and Sullivan escapes with the ledgers; as Sullivan flees, Maguire shoots him in his left arm.

When his father collapses from his wound, Michael Jr. drives his father to a farm, where a childless elderly couple help him recover. Sullivan bonds with his son and discovers from the ledgers that Connor has been embezzling from his father for years, using the names of dead men. As the Sullivans depart, they give the couple much of the stolen money. Sullivan confronts Rooney with the information while they attend Mass. Rooney already knew about the embezzlement and that Connor was likely to die, if not by Sullivan's hand then by the Chicago Outfit once Rooney dies. He still refuses to give up his son. He encourages Sullivan to leave with Michael Jr.

Later one night, cloaked by darkness and rain, Sullivan kills Rooney's entire entourage with his Thompson submachine gun and walks up to Rooney. As Rooney mutters that he is glad his killer is Sullivan, a reluctant Sullivan pulls the trigger. Seeing no further reason to protect Connor, Nitti reveals his location, after making Sullivan promise to end the feud. Sullivan goes to the hotel where Connor is hiding and kills him.

Sullivan drives his son to stay at his Aunt Sara's beach house in Perdition, a town on the shore of Lake Michigan. However, he is ambushed and shot by a disfigured Maguire. As Maguire prepares to photograph the dying Sullivan, Michael Jr. appears and points a gun at Maguire but cannot muster the will to fire. Sullivan pulls out his gun and kills Maguire, before dying in his son's arms. Mourning his father's death, Michael Jr. returns to live with the elderly farm couple. Growing up, Michael, Jr. reflects that his father's only fear was that his son would become like him. Michael states he has never held a gun since the fatal encounter between Maguire and his father. When asked if Sullivan was a good or bad man, he replies "he was my father."